WWI closed trading for a long time and the market fell 25% on the day when trading resumed, but I don't know how big the gap down was - probably quite large. The October 1987 crash caused a 50% overnight gap down on several markets like Japan, Hong Kong.
So based on precedent, the most you can lose on a gap is at least 50%.
However, neither the 1987 crash and WWI were black swans as they gave plenty of warnings - 1987 was after major support had been broken and was during a strong downtrend, and the Friday before was very skittish; WWI took quite a while (1 month) to break out after the assassination of Franz Ferdinand, and the Austro-Hungarian empire made clear warnings before declaring war on Serbia.
Basically, a good trader should have at least been aware of the risk of such large gaps and taken steps to reduce the downside risk if going long during those 2 situations. Still, if you are one of those traders who wilfully ignore fundamentals, then you will run the risk of getting blindsided by a gap like that. And there's always the possibility of a truly surprise event outside market hours.